US5539137A - Aryl substituted silicone fluids having high refractive indices and method for making - Google Patents
Aryl substituted silicone fluids having high refractive indices and method for making Download PDFInfo
- Publication number
- US5539137A US5539137A US08/472,797 US47279795A US5539137A US 5539137 A US5539137 A US 5539137A US 47279795 A US47279795 A US 47279795A US 5539137 A US5539137 A US 5539137A
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/89—Polysiloxanes
- A61K8/896—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate
- A61K8/897—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate containing halogen, e.g. fluorosilicones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/89—Polysiloxanes
- A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/21—Cyclic compounds having at least one ring containing silicon, but no carbon in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
Definitions
- the present invention relates to the synthesis of aryl substituted silicone fluids by the hydrosilylation of an aryl substituted acetylene, such as phenylacetylene or diphenylacetylene with a hydride-functionalized silicone fluid.
- Silicones fluids having a high refractive index are of interest to the hair care products industry.
- silicones having a high refractive index can offer a maximum amount of sheen to hair.
- arylsiloxy units into organopolysiloxanes.
- One method is based on the use of a convenient source of arylsiloxy such as a polydiorganosiloxane having siloxy units with phenyl radicals attached to silicon by carbon-silicon linkages.
- aryl radicals such as a styrl substituent
- hydrosilylation reaction is also another alternative for increasing arylsilicon substitution.
- arylacetylenes such as phenylacetylene
- arylacetylenes can undergo facile hydrosilylation with monomeric silylhydrides.
- Diphenylacetylene has been shown by M. Tanaka et al. Bull. Soc. Fr. 1992, 129, 667.b, to undergo dehydrogenative double silylation with a bis(hydrosilane) to give a cyclic unsaturated compounds as the major product.
- the present invention is based on the discovery that aryl substituted silicone fluids having high indices of refraction and a viscosity in the range of 100 to 40,000 centipoise at 25° C., and preferably 1 00 to 20,000 at 25° C., can be made by the hydrosilylation of arylacetylenes.
- R is a C.sub.(6-13) monovalent aryl radical, and R 1 is hydrogen or an R radical, can be hydrosilylated with a member selected from the group consisting of,
- R 2 is a monovalent radical selected from the group of hydrogen and a C.sub.(1-13) monovalent organic radical
- R 3 is a C.sub.(1-13) monovalent organic radical, and from 1 to 100 chemically combined disiloxy units selected from the group consisting of organohydridosiloxy units
- a (3-8) cyclic hydridosiloxane consisting essentially of a member selected from the group consisting of the organohydridosiloxy units of (a) and a mixture of such organohydridosiloxy units and the diorganosiloxy units of (a).
- the aryl substituted silicone fluids include aryl substituted silicone fluids having a conjugated aryl group either in the form of a styryl or styrenyl group, in instances where R 1 in formula 1 is hydrogen, and a diaryl group, such as a stilbene group, where R 1 in formula 1 is R.
- R 1 in formula 1 is hydrogen
- R 1 in formula 1 is R 1 in formula 1
- R 1 in formula 1 is R.
- the presence of such conjugated groups has been found to enhance the refractive index of such silicone fluids.
- an aryl substituted silicone fluid having a viscosity in the range of about 100 to about 40,000 centipoise at 25° C., and a refractive index of at least 1.5, comprising chemically combined diorganosiloxy units of the formula,
- Q is a conjugated monovalent aryl radical selected from the group consisting of alkenyl substituted C.sub.(6-13) monoaryl radicals, and alkenyl substituted diC.sub.(6-13) aryl radicals, and R 3 is as previously defined.
- an aryl substituted silicone fluid having a refractive index of at least 1.5 comprising effecting the hydrosilylation of an arylacetylene of formula (1), with a linear hydridosiloxane having from 1 to about 80 chemically combined disiloxy units selected from the group consisting of formulas 2 and 3, or 2 and a mixture of 3 and 4, or a (3-8) cyclic hydridosiloxane consisting essentially of chemically combined units of formula 3, or a mixture of 3 and 4.
- Radicals which are included within R of formula 1, are phenyl, tolyl, xylyl, and naphthyl, and preferably phenyl; haloaryl, such as chlorophenyl, alkoxy aryl such as methoxy phenyl, and nitro aryl are also included.
- radicals included within R 2 , and organo radicals of R 3 are for example, C.sub.(1-8) alkyl radicals, such as methyl, ethyl, propyl, butyl and pentyl; haloalkyl for example trifluoropropyl; alkenyl radicals such as vinyl, and propenyl; cycloalkenyl, for example cyclohexenyl; C.sub.(6-13) aryl radicals such as phenyl, tolyl, xylyl, and naphthyl, and preferably phenyl, methoxyphenyl; haloaryl, such as chlorophenyl.
- alkyl radicals such as methyl, ethyl, propyl, butyl and pentyl
- haloalkyl for example trifluoropropyl
- alkenyl radicals such as vinyl, and propenyl
- cycloalkenyl for example cyclohe
- the arylacetylenes of formula (1) are for example, phenylacetylene, diphenylacetylene, and the corresponding chloro, nitro, and methoxy derivatives. Additional arylacetylenes, such as arylacetylene compounds having substituents shown for R, are also included.
- the linear hydridosiloxane having terminal units of formula (2) which consist essentially of disiloxy units shown by formulas (3) and (4), are preferably polydisiloxanes having terminal dimethylhydrogensiloxy units or trimethylsiloxy units, which linear hydridosiloxane can consists essentially of methylhydrogensiloxy units, or a mixture of methylhydrogensiloxy units and dimethylsiloxy units.
- These linear hydridosiloxanes preferably have from about 1 to about 80 disiloxy units and 0.2% to 1.6% of chemically combined hydrogen.
- the cyclic polydimethylsiloxanes are preferably cyclic trimer, tetramer and pentamer.
- the aryl substituted silicone fluids can have a viscosity in the range of about 100 to about 20,000 centipoise at 25° C., depending on such factors as the nature of the substituents attached to silicon in the polydiorganosiloxane backbone, the linear length or cyclic size of the silicon hydride fluid used in the preparation of the fluid, the viscosities of the respective fluids can vary widely. For example, in instances where the fluid backbone is linear and substituted with hexane groups and phenylacetylene, or diphenylacetylene groups, a viscosity of about 100 to about 32,000 centipoise at 25° C. is not unusual.
- the aryl substituted silicone fluids can be made by the hydrosilylation of arylacetylene with the hydridosiloxane fluid, or by the hydrosilylation of hydrolyzable silanes followed by cohydrolysis with appropriate diorganosilanes, such as dimethyldichlorosilane.
- platinum group metal catalyst such as chloroplatinic acid, finely divided platinum metal, and platinum catalyst shown by Ashby, U.S. Pat. No. 3,159,601 and Karstedt, U.S. Pat. No. 3,775,452.
- An effective amount of platinum catalyst is 5 ppm to 200 ppm of Pt based on the weight of the hydrosilylation mixture.
- a temperature in the range of 25° C. to 150° C. can be used.
- An inert organic solvent is optional. Suitable inert solvents are cyclohexane, 2-propanol, toluene, hexane and heptane.
- the product was a phenyl silicone fluid and useful as a hair product component.
- a procedure similar to example 1 was performed, except that a poly(methylhydrido)siloxane fluid was used having 3.79 mol of Si-H and an average of about 80 methyhydridosiloxy units, 450 g of phenylacetylene, 280 g of a solvent in the form of a mixture of C 12 branched alkanes.
- the mixture was heated at 8 hours at 75° C., and at 80° C. for 2 additional hours using a total of 99 ppm of Pt catalyst. There was obtained 60 g of an orange, slightly hazy fluid having a viscosity of 32,000 centipoise and an R.I. of 1.5720.
- a procedure similar to example 2 was carried out, except that there was added over a period of one hour, 231g (3.79 tool Sill) of a linear hydridosiloxane having an average of about 15 methylhydridosiloxy units and terminal hydridodimethylsiloxy units to a mixture at 55° C. of 450 g of phenylacetylene, 280 g of a mixture of C 12 branched alkanes as a solvent, and 250 ppm of Pt.
- the reaction mixture was heated at 75° C. for 15 hours and then heated an additional five hours at 80° C. in the presence of an additional 39 ppm of Pt.
- Vacuum distillation at 75° C. provided an orange, slightly hazy fluid having a viscosity of 6000 centipoise at 25° C. and an R.I. of 1.5745.
Abstract
Description
R-C C-R.sup.1, (1)
R.sup.2 (R.sup.3).sub.2 SiO.sub.1/2, (2)
H(R.sup.3) SiO, (3)
(R.sup.3).sub.2 SiO, (4)
QR.sup.3 SiO, (5)
Claims (11)
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/472,797 US5539137A (en) | 1995-06-07 | 1995-06-07 | Aryl substituted silicone fluids having high refractive indices and method for making |
JP8135618A JPH09136960A (en) | 1995-06-07 | 1996-05-30 | Aryl-substituted silicone fluid having high refractive indexand method for preparing it |
GB9611442A GB2301828B (en) | 1995-06-07 | 1996-05-31 | Aryl substituted silicone fluids having high refractive indices and method for making |
DE19622142A DE19622142A1 (en) | 1995-06-07 | 1996-06-01 | Aryl substituted silicone fluids with high refractive index and process for their preparation |
FR9606967A FR2735135B1 (en) | 1995-06-07 | 1996-06-06 | SILICONE FLUIDS SUBSTITUTED BY ARYL GROUPS WITH HIGH REFRACTION INDICES AND THEIR MANUFACTURING PROCESS |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/472,797 US5539137A (en) | 1995-06-07 | 1995-06-07 | Aryl substituted silicone fluids having high refractive indices and method for making |
Publications (1)
Publication Number | Publication Date |
---|---|
US5539137A true US5539137A (en) | 1996-07-23 |
Family
ID=23876986
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US08/472,797 Expired - Lifetime US5539137A (en) | 1995-06-07 | 1995-06-07 | Aryl substituted silicone fluids having high refractive indices and method for making |
Country Status (5)
Country | Link |
---|---|
US (1) | US5539137A (en) |
JP (1) | JPH09136960A (en) |
DE (1) | DE19622142A1 (en) |
FR (1) | FR2735135B1 (en) |
GB (1) | GB2301828B (en) |
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1999033433A2 (en) * | 1997-12-23 | 1999-07-08 | Henkel Kommanditgesellschaft Auf Aktien | Hair treatment products |
EP1101786A1 (en) * | 1999-11-22 | 2001-05-23 | General Electric Company | Process for the preparation of silicone fluids |
WO2003011944A2 (en) * | 2001-07-28 | 2003-02-13 | Dow Corning Corporation | High refractive index polysiloxanes and their preparation |
EP1334991A1 (en) * | 2002-02-08 | 2003-08-13 | Ophtec B.V. | High refractive index flexible silicone |
WO2003066707A1 (en) * | 2002-02-08 | 2003-08-14 | Ophtec B.V. | High refractive index flexible silicone |
US20030162929A1 (en) * | 2002-02-08 | 2003-08-28 | Verbruggen Miriam Adrienne Lambertina | High refractive index flexible silicone |
US20060287455A1 (en) * | 2005-06-15 | 2006-12-21 | Bausch & Lomb Incorporated | High refractive-index, hydrophilic, arylsiloxy-containing macromonomers and polymers, and ophthalmic devices comprising such polymers |
US20060286147A1 (en) * | 2005-06-15 | 2006-12-21 | Bausch & Lomb Incorporated | High refractive-index, hydrophilic, arylsiloxy-containing monomers and polymers, and ophthalmic devices comprising such polymers |
US20100041823A1 (en) * | 2008-08-13 | 2010-02-18 | Designer Molecules, Inc. | Novel siloxane monomers and methods for use thereof |
US9422315B2 (en) | 2014-12-05 | 2016-08-23 | Momentive Performance Materials Japan Llc | Organosiloxane composition having high refractive index and applications containing the same |
CN114149587A (en) * | 2021-12-30 | 2022-03-08 | 烟台德邦科技股份有限公司 | UV-curable phenyl vinyl polysiloxane and synthesis thereof and preparation method of adhesive |
CN117209765A (en) * | 2023-10-08 | 2023-12-12 | 华东理工大学 | Silicon-containing aryne resin and preparation method and application thereof |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP5813357B2 (en) * | 2011-04-19 | 2015-11-17 | 株式会社カネカ | Curable composition |
Citations (8)
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US3159662A (en) * | 1962-07-02 | 1964-12-01 | Gen Electric | Addition reaction |
US3775452A (en) * | 1971-04-28 | 1973-11-27 | Gen Electric | Platinum complexes of unsaturated siloxanes and platinum containing organopolysiloxanes |
US4079070A (en) * | 1975-08-13 | 1978-03-14 | Bayer Aktiengesellschaft | Preparation of cyclic diphenylsiloxanes |
US4599440A (en) * | 1984-09-26 | 1986-07-08 | Toshiba Silicone Co., Ltd. | Organocyclosiloxane |
US5041594A (en) * | 1989-08-18 | 1991-08-20 | Wacker-Chemie Gmbh | Process for preparing organo(poly)siloxanes having Si-linked, conjugated dienyl groups |
US5304667A (en) * | 1990-07-12 | 1994-04-19 | Consortium Fur Elektrochemische Industrie Gmbh | Cyclosiloxanes containing mesogenic side groups |
US5329036A (en) * | 1992-09-02 | 1994-07-12 | Hughes Aircraft Company | (alpha, omega)phenylethynyl siloxane monomers, oligomers, and polymers thereof |
US5412055A (en) * | 1993-04-19 | 1995-05-02 | Hercules Incoporated | Fully substituted cyclopolysiloxanes and their use for making organosilicon polymers |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4447633A (en) * | 1983-06-14 | 1984-05-08 | North Dakota State University | Ultrasonically promoted hydrosilations |
US4807968A (en) * | 1986-10-27 | 1989-02-28 | Hoechst Celanese Corp. | Polymer blends exhibiting nonlinear optical response |
US4801659A (en) * | 1986-10-27 | 1989-01-31 | Hoechst Celanese Corp. | Organopolysiloxanes exhibiting nonlinear optical response |
-
1995
- 1995-06-07 US US08/472,797 patent/US5539137A/en not_active Expired - Lifetime
-
1996
- 1996-05-30 JP JP8135618A patent/JPH09136960A/en not_active Withdrawn
- 1996-05-31 GB GB9611442A patent/GB2301828B/en not_active Expired - Fee Related
- 1996-06-01 DE DE19622142A patent/DE19622142A1/en not_active Withdrawn
- 1996-06-06 FR FR9606967A patent/FR2735135B1/en not_active Expired - Fee Related
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3159662A (en) * | 1962-07-02 | 1964-12-01 | Gen Electric | Addition reaction |
US3775452A (en) * | 1971-04-28 | 1973-11-27 | Gen Electric | Platinum complexes of unsaturated siloxanes and platinum containing organopolysiloxanes |
US4079070A (en) * | 1975-08-13 | 1978-03-14 | Bayer Aktiengesellschaft | Preparation of cyclic diphenylsiloxanes |
US4599440A (en) * | 1984-09-26 | 1986-07-08 | Toshiba Silicone Co., Ltd. | Organocyclosiloxane |
US5041594A (en) * | 1989-08-18 | 1991-08-20 | Wacker-Chemie Gmbh | Process for preparing organo(poly)siloxanes having Si-linked, conjugated dienyl groups |
US5304667A (en) * | 1990-07-12 | 1994-04-19 | Consortium Fur Elektrochemische Industrie Gmbh | Cyclosiloxanes containing mesogenic side groups |
US5329036A (en) * | 1992-09-02 | 1994-07-12 | Hughes Aircraft Company | (alpha, omega)phenylethynyl siloxane monomers, oligomers, and polymers thereof |
US5412055A (en) * | 1993-04-19 | 1995-05-02 | Hercules Incoporated | Fully substituted cyclopolysiloxanes and their use for making organosilicon polymers |
Cited By (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1999033433A3 (en) * | 1997-12-23 | 1999-09-02 | Henkel Kgaa | Hair treatment products |
WO1999033433A2 (en) * | 1997-12-23 | 1999-07-08 | Henkel Kommanditgesellschaft Auf Aktien | Hair treatment products |
EP1101786A1 (en) * | 1999-11-22 | 2001-05-23 | General Electric Company | Process for the preparation of silicone fluids |
WO2003011944A2 (en) * | 2001-07-28 | 2003-02-13 | Dow Corning Corporation | High refractive index polysiloxanes and their preparation |
WO2003011944A3 (en) * | 2001-07-28 | 2003-05-08 | Dow Corning | High refractive index polysiloxanes and their preparation |
US20040236057A1 (en) * | 2001-07-28 | 2004-11-25 | Pierre Chevalier | High refractive index polysiloxanes and their preparation |
US7429638B2 (en) | 2001-07-28 | 2008-09-30 | Dow Corning Limited | High refractive index polysiloxanes and their preparation |
US7217778B2 (en) | 2002-02-08 | 2007-05-15 | Ophtec B.V. | High refractive index flexible silicone |
EP1334991A1 (en) * | 2002-02-08 | 2003-08-13 | Ophtec B.V. | High refractive index flexible silicone |
WO2003066707A1 (en) * | 2002-02-08 | 2003-08-14 | Ophtec B.V. | High refractive index flexible silicone |
US20030162929A1 (en) * | 2002-02-08 | 2003-08-28 | Verbruggen Miriam Adrienne Lambertina | High refractive index flexible silicone |
US20060286147A1 (en) * | 2005-06-15 | 2006-12-21 | Bausch & Lomb Incorporated | High refractive-index, hydrophilic, arylsiloxy-containing monomers and polymers, and ophthalmic devices comprising such polymers |
US7297160B2 (en) | 2005-06-15 | 2007-11-20 | Bausch & Lomb Incorporated | High refractive-index, hydrophilic, arylsiloxy-containing macromonomers and polymers, and ophthalmic devices comprising such polymers |
US20060287455A1 (en) * | 2005-06-15 | 2006-12-21 | Bausch & Lomb Incorporated | High refractive-index, hydrophilic, arylsiloxy-containing macromonomers and polymers, and ophthalmic devices comprising such polymers |
US7632904B2 (en) | 2005-06-15 | 2009-12-15 | Bausch & Lomb Incorporated | High refractive-index, hydrophilic, arylsiloxy-containing monomers and polymers, and ophthalmic devices comprising such polymers |
US20100041823A1 (en) * | 2008-08-13 | 2010-02-18 | Designer Molecules, Inc. | Novel siloxane monomers and methods for use thereof |
US8008419B2 (en) * | 2008-08-13 | 2011-08-30 | Designer Molecules, Inc. | Siloxane monomers and methods for use thereof |
US9422315B2 (en) | 2014-12-05 | 2016-08-23 | Momentive Performance Materials Japan Llc | Organosiloxane composition having high refractive index and applications containing the same |
CN114149587A (en) * | 2021-12-30 | 2022-03-08 | 烟台德邦科技股份有限公司 | UV-curable phenyl vinyl polysiloxane and synthesis thereof and preparation method of adhesive |
CN117209765A (en) * | 2023-10-08 | 2023-12-12 | 华东理工大学 | Silicon-containing aryne resin and preparation method and application thereof |
CN117209765B (en) * | 2023-10-08 | 2024-03-12 | 华东理工大学 | Silicon-containing aryne resin and preparation method and application thereof |
Also Published As
Publication number | Publication date |
---|---|
GB9611442D0 (en) | 1996-08-07 |
FR2735135A1 (en) | 1996-12-13 |
JPH09136960A (en) | 1997-05-27 |
GB2301828A (en) | 1996-12-18 |
FR2735135B1 (en) | 1998-08-21 |
GB2301828B (en) | 1999-02-24 |
DE19622142A1 (en) | 1996-12-12 |
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